2-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide → HCID 86634007, compound

HRID 1041337Notes

Reaction equation

HRID 1041337 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[N:6]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:7][CH2:8][C:9](=[O:12])[NH:10][CH2:11][C:4]=2[CH:3]=1.Cl[C:22]1[N:27]=[C:26]([NH:28][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([NH:33][CH3:34])=[O:32])[C:25]([Cl:39])=[CH:24][N:23]=1>>[Cl:39][C:25]1[C:26]([NH:28][C:29]2[CH:38]=[CH:37][CH:36]=[CH:35][C:30]=2[C:31]([NH:33][CH3:34])=[O:32])=[N:27][C:22]([NH:1][C:2]2[CH:20]=[CH:19][C:5]3[N:6]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:7][CH2:8][C:9](=[O:12])[NH:10][CH2:11][C:4]=3[CH:3]=2)=[N:23][CH:24]=1

Participants

3

Reactant 2

HCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamideHCID 86634008HCID 86634008, compound

Product 1

HCID 86634007HCID 86634007, compound

Procedure

2-{5-Chloro-2-[4-oxo-1-(2,2,2-trifluoro-acetyl)-1,2,3,4,5,6-hexahydro-benzo[b][1,5]diazocin-8-ylamino]-pyrimidin-4-ylamino}-N-methyl-benzamide was prepared from 8-Amino-1-(2,2,2-trifluoro-acetyl)-2,3,5,6-tetrahydro-1H-benzo[b][1,5]diazocin-4-one and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide in an analogous manner to Example 1221d. Title compound isolated as an off-white solid (27 mg, 14%). mp 191-194° C.; LCMS: m/z=548.25 (M+H+), HPLC (98% purity), 1H NMR (400 MHz, DMSO-d6) δ 11.69 (s, 1H), 9.78 (s, 1H), 8.72 (m, 2H), 8.27 (s, 1H), 7.90 (m, 1H), 7.77 (d, J=8.1 Hz, 1H), 7.71 (s, 1H), 7.66 (d, J=8.6 Hz, 1H), 7.46 (t, J=8.3 Hz, 1H), 7.29 (d, J=8.3 Hz, 1H), 7.16 (t, J=7.8 Hz, 1H), 4.65 (m, 1H), 4.43 (m, 1H), 3.70 (m, 1H), 3.18 (m, 1H), 2.81 (m, 4H), 2.36 (m, 1H).

Sources & evidence

ORD record
ord-c10f00da0b444a21826531115af9de2b
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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